508 & 512 E Winchester Ave
Middlesboro, KY 40965
2 Beds
2 Baths
6,696 sqft (on 0.55 acres)
$960,000
$960,000
2 Beds
2 Baths
6,696 sqft
(on 0.55 acres)
Local Information
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Description
Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to acquire substantial rental inventory in one convenient location. Built for efficiency and scale, each building offers significant square footage ideal for multiple residential units, making them well-suited for investors seeking strong cash flow potential in the Middlesboro market. The generous lot sizes allow for ample parking, green space, or future expansion opportunities. Situated along Winchester Avenue, the properties benefit from convenient access to local amenities, major thoroughfares, and the broader Middlesboro community. Whether you're an experienced multifamily investor or looking to expand your portfolio, this paired offering represents a solid foundation for long-term rental income and value appreciation.
Home Highlights
Parking
12 Parking Spaces
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$143
Listed
75 days ago
Home Details for 508 & 512 E Winchester Ave
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Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 6696 Square Feet |
Appliances & Utilities Laundry: Electric Dryer Hookup,Washer Hookup |
Heating & Cooling Heating: ElectricHas CoolingAir Conditioning: ElectricHas HeatingHeating Fuel: Electric |
Levels, Entrance, & Accessibility Number of Stories: 2 |
Security Security: Fire Sprinkler System |
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Exterior Home Features Roof: Shingle |
Parking & Garage Parking Spaces: 12 |
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Days on Market: 75 |
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Year Built Year Built: 1980 |
Property Type / Style Property Type: Residential IncomeProperty Subtype: Multi Family |
Property Information Parcel Number: 0694206012.00 069.42.06.011.00 |
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Price List Price: $960,000Price Per Sqft: $143 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: Active |
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Direction & Address City: MiddlesboroCommunity: City Limits |
School Information High School: Middlesboro IndHigh School District: Bell County - 87 |
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Listing Agent Listing ID: 26007224 |
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Building Area Building Area: 6696 Square Feet |
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Lot Area: 0.55 acres |
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Listing Terms: Cash, Conventional |
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Mls Number: 26007224 |
Last check for updates: about 5 hours ago
Listing courtesy of Beth Combs, (606) 269-1807
Turn Key Realty
Source: Imagine MLS, MLS#26007224
Also Listed on Imagine MLS.
Market trends in Middlesboro
Last updated May 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
46
10MoM
Price History for 508 & 512 E Winchester Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 04/07/2026 | $960,000 | Listed For Sale | Imagine MLS #26007224 |
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Comparable Sales for 508 & 512 E Winchester Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Multi-Family Home | $167,000 | 10/01/25 | 2 | 2 | 1,608 | |
0.54 | Multi-Family Home | $2,750,000 | 06/01/26 | 99 | 58 | 50,352 | |
4.97 | Multi-Family Home | $325,000 | 10/06/25 | - | - |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETREMAX PROFESSIONAL'S
OFF MARKETColdwell Banker Bisceglia Realty & Auction Co, Imagine MLS
OFF MARKETColdwell Banker Bisceglia Real
OFF MARKETAction Realty, Imagine MLS
OFF MARKETColdwell Banker Bisceglia Real
FOR SALE1.69 ACRESColdwell Banker Bisceglia Realty & Auction Co, Imagine MLS
FOR SALE0.25 ACRESTurn Key Realty, Imagine MLS
Assigned Schools
These are the assigned schools for 508 & 512 E Winchester Ave.
- Middlesboro Elementary School
- PK-4
- Public
- 499 Students
5/10GreatSchools RatingParent Rating AverageThis school does not want to deal with parents, so they make it to where parents cannot get involved. They schedule parent teacher conferences in the hours of you work you cannot attend. They also only give notice a few days in advance so requesting time off work in order to attend is impossible. If you do get to attend you speak to the teacher for a total of 5minutes before you are forced out. Policies are constantly changing and of course parents are never made aware of the changes.Parent Review8y ago - Middlesboro Middle School
- 5-8
- Public
- 285 Students
5/10GreatSchools RatingParent Rating AverageWe think our daughter receives a great education at at MHS. The teachers are highly-skilled and the school has many resources and extracurricular activities. She has done very well on her college entrance exams and plans to go to top college. I question this site's rating system if it does not give this wonderful school and community a great rating.Parent Review11y ago - Middlesboro High School
- 9-12
- Public
- 319 Students
6/10GreatSchools RatingParent Rating AverageWe think our daughter receives a great education at at MHS. The teachers are highly-skilled and the school has many resources and extracurricular activities. She has done very well on her college entrance exams and plans to go to a top college. I question this site's rating system if it does not give this wonderful school and community a great rating.Parent Review11y ago 
Check out schools near 508 & 512 E Winchester Ave.
What Locals Say about Middlesboro
At least 43 Trulia users voted on each feature.
93 % Say car is needed
87 % Say yards are well-kept
81 % Say parking is easy
79 % Say there's holiday spirit
71 % Say kids play outside
68 % Say it's dog friendly
61 % Say they plan to stay for at least 5 years
58 % Say there's wildlife
54 % Say neighbors are friendly
52 % Say people would walk alone at night
49 % Say it's quiet
44 % Say there are sidewalks
40 % Say it's walkable to restaurants
37 % Say streets are well-lit
28 % Say there are community events
27 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Beth Combs, Turn Key Realty
Agent Phone: (606) 269-1807
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
508 & 512 E Winchester Ave, Middlesboro, KY 40965 is a 2 bedroom, 2 bathroom, 6,696 sqft multi-family built in 1980. This property is currently available for sale and was listed by Imagine MLS on Apr 7, 2026. The MLS # for this home is MLS# 26007224.